(2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 210479-85-9

• 英文名称: (2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3R,4R,5S)-2-(acetamidomethyl)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 210479-85-9
• 化学式: C₂₇H₃₆N₂O₆
• 分子量: 484.593
• InChiKey: SUHCYXYGRREALB-ZFFYZDHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-glucuronic acid 、 (2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到(2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of d-glucose with 6-amino-6-deoxy-2,5-imino-d-glucitol

  摘要：

  Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C-2 symmetric bis-aziridine deriving from D-mannitol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00817-x
• 作为产物：
  描述：

  1-O-acetyl-3,4-di-O-benzyl-6-[(tert-butyloxycarbonyl)amino]-2,5-[(tert-butyloxycarbonyl)imino]-2,5,6-trideoxy-D-glucitol 在 sodium methylate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2R,3R,4R,5S)-2-(Acetylamino-methyl)-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of ester-and amide-linked pseudo-azadisaccharides via coupling of d-glucose with 6-amino-6-deoxy-2,5-imino-d-glucitol

  摘要：

  Hydrolytically-resistant pseudodisaccharides incorporating an azafuranose have been prepared by coupling 6-amino-2,5-imino-D-glucitol derivatives with D-glucose, either through an ester or an amide bond. Synthesis of the azasugar templates was achieved by nucleophilic opening of a C-2 symmetric bis-aziridine deriving from D-mannitol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00817-x